(2R/S)-6-PNG (6-Prenylnaringenin) is a potent and reversible Cav3.2 T-type Ca2+ channel (T channel) blocker. (2R/S)-6-PNG can cross the BBB (blood-brain barrier). (2R/S)-6-PNG inhibits neuropathic and visceral pain in mice.

Physicochemical Properties

Molecular Formula	C20H20O5
Molecular Weight	340.3698
Exact Mass	340.131
CAS #	68682-01-9
Related CAS #	(2S)-6-Prenylnaringenin;68236-13-5
PubChem CID	3519901
Appearance	White to off-white solid powder
Melting Point	209 - 209.5 °C
LogP	4.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	25
Complexity	504
Defined Atom Stereocenter Count	0
SMILES	O1C2C([H])=C(C(C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])[H])=C(C=2C(C([H])([H])C1([H])C1C([H])=C([H])C(=C([H])C=1[H])O[H])=O)O[H])O[H]
InChi Key	YHWNASRGLKJRJJ-UHFFFAOYSA-N
InChi Code	InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9,17,21-22,24H,8,10H2,1-2H3
Chemical Name	5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In differentiated NG108-15 cells, (2R/S)-6-PNG (6-Prenylnaringenin) does not significantly affect voltage-gated Na+ channels or high-voltage-activated Ca2+ channels [1]. However, it can effectively block Cav3.2. The inhibitory potency of (2R/S)-6-PNG on Cav3.2 and HVA currents has an IC50 value of 5.20; consequently, the ratio of Cav3.2 and Nav currents is 3.54 (Cav3.2/Nav)[1].
ln Vivo	(2R/S)-6-PNG (6-prenylnaringenin; 10-30 mg/kg; i.p.; single dose; 15 min before Na2S) greatly lowers Na2S-induced intracolonic Nociceptive behavior and/or related hyperalgesia (i.col.) Administration of Na2S (an H2S donor) [1]. (2R/S)-6-PNG (30 mg/kg; i.p.) reduced the rise in the number of phosphorylated ERK-positive cells following i.col. Primary afferent neurons project to Na2S in layers I-II, V-VI and X, and Na2S generates an increase in the number of phosphorylated ERK-positive cells [1]. (2R/S)-6-PNG (0.01-1 and 0.1-10 nmol/paw; intraplantar injection) reversed mechanical damage caused by partial sciatic nerve ligation (PSNL) and intraperitoneal treatment of oxaliplatin (OHP)a, respectively Allodynia is dose-dependent [1]. (2R/S)-6-PNG (20-30 mg/kg; i.p.) effectively corrected PSNL-induced allodynia. (2R/S)-6-PNG (10-20 mg/kg; i.p.) effectively reverses OHP-induced allodynia (5 mg/kg; i.p.; single dose) [1].
References	[1]. Blockade of T-type calcium channels by 6-prenylnaringenin, a hop component, alleviates neuropathic and visceral pain in mice. Neuropharmacology.
Additional Infomation	(S)-4',5,7-Trihydroxy-6-prenylflavanone is a member of flavanones. (S)-4',5,7-Trihydroxy-6-prenylflavanone has been reported in Psoralea and Sophora tomentosa with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~125 mg/mL (~367.25 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (6.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (6.11 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (6.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.9380 mL	14.6899 mL	29.3798 mL
	5 mM	0.5876 mL	2.9380 mL	5.8760 mL
	10 mM	0.2938 mL	1.4690 mL	2.9380 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.